3-Fluoro-salicylaldoxime at 6.5 GPa.

3-Fluoro-salicylaldoxime, C(7)H(6)FNO(2), unlike many salicylaldoxime derivatives, forms a crystal structure containing hydrogen-bonded chains rather than centrosymmetric hydrogen-bonded ring motifs. Each chain inter-acts with two chains above and two chains below via π-π stacking contacts [shortest centroid-centroid distance = 3.295 (1) Å]. This structure at 6.5 GPa represents the final point in a single-crystal compression study.

Related literature

For salicylaldoximes with bulky side groups which more commonly form hydrogen-bonded chains, see: Koziol & Kosturkiewicz (1984 ▶); Maurin (1994 ▶). For salicylaldoximes without bulky side groups that form chains, see: Wood et al. (2007a ▶,b ▶); Wood, Forgan, Parsons et al. (2006 ▶). For high pressure studies on salicyl­aldoximes, see: Wood et al. (2008 ▶, 2009 ▶); Wood, Forgan, Henderson et al. (2006 ▶). For specialized equipment used in the high pressure study, see: Merrill & Bassett (1974 ▶); Piermarini et al. (1975 ▶).

Experimental

Crystal data

C7H6FNO2

M = 155.13

Orthorhombic,

a = 6.156 (2) Å

b = 9.751 (3) Å

c = 8.6764 (18) Å

V = 520.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 298 K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2006 ▶) T min = 0.39, T max = 0.98

2715 measured reflections

333 independent reflections

233 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.049

S = 0.94

305 reflections

106 parameters

94 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; method used to solve structure: model taken from ambient pressure structure (Wood et al., 2007b ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029043/tk2511sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029043/tk2511Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H6FNO2	F(000) = 320
Mr = 155.13	Dx = 1.978 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 779 reflections
a = 6.156 (2) Å	θ = 3–24°
b = 9.751 (3) Å	µ = 0.17 mm−1
c = 8.6764 (18) Å	T = 298 K
V = 520.8 (3) Å3	Block, pale-yellow
Z = 4	0.15 × 0.12 × 0.10 mm

Bruker APEXII diffractometer	233 reflections with I > 2σ(I)
graphite	Rint = 0.074
ω scans	θmax = 27.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2006)	h = −6→6
Tmin = 0.39, Tmax = 0.98	k = −10→10
2715 measured reflections	l = −10→10
333 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.036	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are 12.4 13.8 4.45 -0.254
wR(F2) = 0.049	(Δ/σ)max < 0.001
S = 0.94	Δρmax = 0.16 e Å−3
305 reflections	Δρmin = −0.18 e Å−3
106 parameters	Extinction correction: Larson (1970), Equation 22
94 restraints	Extinction coefficient: 119.189
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	0.4779 (9)	0.1918 (6)	0.9058 (5)	0.0268
N2	0.4588 (11)	0.1849 (7)	0.7440 (5)	0.0247
C3	0.4049 (11)	0.3001 (7)	0.6852 (7)	0.0191
C4	0.3841 (12)	0.3034 (7)	0.5185 (6)	0.0157
C5	0.3721 (11)	0.1828 (9)	0.4328 (5)	0.0143
O5	0.3858 (9)	0.0571 (5)	0.4956 (5)	0.0214
C6	0.3455 (12)	0.1950 (9)	0.2755 (6)	0.0201
F6	0.3356 (7)	0.0740 (5)	0.1972 (4)	0.0265
C7	0.3246 (12)	0.3167 (8)	0.2001 (7)	0.0185
C8	0.3431 (12)	0.4332 (8)	0.2861 (6)	0.0189
C9	0.3738 (11)	0.4309 (8)	0.4436 (6)	0.0183
H3	0.3781	0.3782	0.7440	0.0230*
H7	0.3014	0.3204	0.0958	0.0219*
H8	0.3343	0.5184	0.2363	0.0227*
H9	0.3877	0.5129	0.4979	0.0218*
H5	0.392 (14)	0.059 (7)	0.594 (4)	0.0321*
H1	0.546 (15)	0.114 (6)	0.929 (7)	0.0400*

	U11	U22	U33	U12	U13	U23
O1	0.037 (5)	0.032 (5)	0.0119 (13)	0.002 (2)	0.0009 (19)	0.003 (2)
N2	0.035 (6)	0.028 (4)	0.0109 (15)	−0.001 (3)	0.001 (2)	0.008 (3)
C3	0.017 (5)	0.022 (4)	0.0176 (17)	0.000 (3)	0.001 (3)	0.001 (2)
C4	0.010 (4)	0.020 (2)	0.0176 (18)	0.001 (2)	−0.002 (3)	0.0018 (16)
C5	0.004 (4)	0.020 (2)	0.0189 (19)	0.000 (2)	0.000 (3)	0.0014 (16)
O5	0.023 (4)	0.022 (2)	0.019 (2)	0.0014 (19)	0.003 (2)	0.0014 (18)
C6	0.022 (6)	0.020 (2)	0.019 (2)	0.000 (3)	−0.001 (3)	−0.0035 (16)
F6	0.035 (3)	0.023 (2)	0.0215 (17)	0.0051 (16)	0.001 (2)	−0.0071 (18)
C7	0.017 (5)	0.024 (3)	0.015 (2)	0.002 (2)	0.002 (3)	−0.0008 (18)
C8	0.022 (5)	0.017 (3)	0.018 (2)	0.000 (2)	0.001 (3)	0.004 (2)
C9	0.022 (5)	0.016 (3)	0.017 (2)	0.005 (2)	0.002 (3)	−0.003 (2)

O1—N2	1.410 (6)	O5—H5	0.86 (4)
O1—H1	0.89 (4)	C6—F6	1.363 (9)
N2—C3	1.278 (9)	C6—C7	1.361 (9)
C3—C4	1.452 (8)	C7—C8	1.365 (10)
C3—H3	0.932	C7—H7	0.917
C4—C5	1.394 (9)	C8—C9	1.380 (8)
C4—C9	1.404 (10)	C8—H8	0.938
C5—O5	1.345 (9)	C9—H9	0.932
C5—C6	1.380 (7)
N2—O1—H1	103 (4)	C5—C6—F6	115.1 (7)
O1—N2—C3	112.2 (7)	C5—C6—C7	124.2 (7)
N2—C3—C4	116.2 (7)	F6—C6—C7	120.8 (5)
N2—C3—H3	123.1	C6—C7—C8	117.1 (6)
C4—C3—H3	120.8	C6—C7—H7	121.6
C3—C4—C5	121.2 (6)	C8—C7—H7	121.3
C3—C4—C9	119.0 (6)	C7—C8—C9	122.6 (8)
C5—C4—C9	119.8 (5)	C7—C8—H8	118.8
C4—C5—O5	123.3 (4)	C9—C8—H8	118.6
C4—C5—C6	117.5 (7)	C4—C9—C8	118.6 (7)
O5—C5—C6	119.1 (7)	C4—C9—H9	121.4
C5—O5—H5	113 (5)	C8—C9—H9	119.9

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5i	0.89 (7)	1.81 (6)	2.684 (8)	165 (7)
O5—H5···N2	0.85 (4)	1.84 (6)	2.530 (7)	137 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5i	0.89 (7)	1.81 (6)	2.684 (8)	165 (7)
O5—H5⋯N2	0.85 (4)	1.84 (6)	2.530 (7)	137 (6)

Symmetry code: (i) .